US3064019A - Process for the production of compounds of polyvalent metals with polychlorophenols and higher carboxylic acids - Google Patents
Process for the production of compounds of polyvalent metals with polychlorophenols and higher carboxylic acids Download PDFInfo
- Publication number
- US3064019A US3064019A US32118A US3211860A US3064019A US 3064019 A US3064019 A US 3064019A US 32118 A US32118 A US 32118A US 3211860 A US3211860 A US 3211860A US 3064019 A US3064019 A US 3064019A
- Authority
- US
- United States
- Prior art keywords
- acid
- water
- sodium
- mol
- polychlorophenol
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 238000000034 method Methods 0.000 title claims description 20
- 229910052751 metal Inorganic materials 0.000 title claims description 18
- 239000002184 metal Substances 0.000 title claims description 18
- 150000001875 compounds Chemical class 0.000 title claims description 13
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- 150000001735 carboxylic acids Chemical class 0.000 title claims description 5
- 150000002739 metals Chemical class 0.000 title description 4
- 150000003839 salts Chemical class 0.000 claims description 22
- 239000007864 aqueous solution Substances 0.000 claims description 15
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical class OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 10
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 claims description 8
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical class CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 5
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 5
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims description 5
- 235000010233 benzoic acid Nutrition 0.000 claims description 5
- 229910052744 lithium Inorganic materials 0.000 claims description 5
- 159000000001 potassium salts Chemical class 0.000 claims description 5
- 229910052708 sodium Inorganic materials 0.000 claims description 5
- 239000011734 sodium Substances 0.000 claims description 5
- HNNQYHFROJDYHQ-UHFFFAOYSA-N 3-(4-ethylcyclohexyl)propanoic acid 3-(3-ethylcyclopentyl)propanoic acid Chemical class CCC1CCC(CCC(O)=O)C1.CCC1CCC(CCC(O)=O)CC1 HNNQYHFROJDYHQ-UHFFFAOYSA-N 0.000 claims description 4
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052725 zinc Inorganic materials 0.000 claims description 4
- 239000011701 zinc Substances 0.000 claims description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Chemical class CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 claims description 3
- RULKYXXCCZZKDZ-UHFFFAOYSA-N 2,3,4,5-tetrachlorophenol Chemical compound OC1=CC(Cl)=C(Cl)C(Cl)=C1Cl RULKYXXCCZZKDZ-UHFFFAOYSA-N 0.000 claims description 3
- LINPIYWFGCPVIE-UHFFFAOYSA-N 2,4,6-trichlorophenol Chemical compound OC1=C(Cl)C=C(Cl)C=C1Cl LINPIYWFGCPVIE-UHFFFAOYSA-N 0.000 claims description 3
- HFZWRUODUSTPEG-UHFFFAOYSA-N 2,4-dichlorophenol Chemical class OC1=CC=C(Cl)C=C1Cl HFZWRUODUSTPEG-UHFFFAOYSA-N 0.000 claims description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Chemical class CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 claims description 3
- XRHGYUZYPHTUJZ-UHFFFAOYSA-N 4-chlorobenzoic acid Chemical class OC(=O)C1=CC=C(Cl)C=C1 XRHGYUZYPHTUJZ-UHFFFAOYSA-N 0.000 claims description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Chemical class CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 claims description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 3
- 239000005639 Lauric acid Chemical class 0.000 claims description 3
- 239000005642 Oleic acid Chemical class 0.000 claims description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Chemical class CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 claims description 3
- 235000021355 Stearic acid Nutrition 0.000 claims description 3
- 229910052782 aluminium Inorganic materials 0.000 claims description 3
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 3
- WDIHJSXYQDMJHN-UHFFFAOYSA-L barium chloride Chemical compound [Cl-].[Cl-].[Ba+2] WDIHJSXYQDMJHN-UHFFFAOYSA-L 0.000 claims description 3
- 229910001626 barium chloride Inorganic materials 0.000 claims description 3
- OZECDDHOAMNMQI-UHFFFAOYSA-H cerium(3+);trisulfate Chemical compound [Ce+3].[Ce+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O OZECDDHOAMNMQI-UHFFFAOYSA-H 0.000 claims description 3
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 3
- 229930195729 fatty acid Natural products 0.000 claims description 3
- 239000000194 fatty acid Substances 0.000 claims description 3
- 150000004665 fatty acids Chemical class 0.000 claims description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Chemical class CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 claims description 3
- RLJMLMKIBZAXJO-UHFFFAOYSA-N lead nitrate Chemical compound [O-][N+](=O)O[Pb]O[N+]([O-])=O RLJMLMKIBZAXJO-UHFFFAOYSA-N 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Chemical class CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical class CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 claims description 3
- 239000008117 stearic acid Chemical class 0.000 claims description 3
- 239000003784 tall oil Chemical class 0.000 claims description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052793 cadmium Inorganic materials 0.000 claims description 2
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 239000011572 manganese Substances 0.000 claims description 2
- 150000003467 sulfuric acid derivatives Chemical class 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 11
- HCJLVWUMMKIQIM-UHFFFAOYSA-M sodium;2,3,4,5,6-pentachlorophenolate Chemical compound [Na+].[O-]C1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl HCJLVWUMMKIQIM-UHFFFAOYSA-M 0.000 description 10
- 239000002253 acid Substances 0.000 description 9
- 239000011280 coal tar Substances 0.000 description 9
- 239000003921 oil Substances 0.000 description 9
- 239000000243 solution Substances 0.000 description 9
- ARUVKPQLZAKDPS-UHFFFAOYSA-L copper(II) sulfate Chemical compound [Cu+2].[O-][S+2]([O-])([O-])[O-] ARUVKPQLZAKDPS-UHFFFAOYSA-L 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- KQSJSRIUULBTSE-UHFFFAOYSA-M sodium;3-(3-ethylcyclopentyl)propanoate Chemical compound [Na+].CCC1CCC(CCC([O-])=O)C1 KQSJSRIUULBTSE-UHFFFAOYSA-M 0.000 description 7
- 239000002904 solvent Substances 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 6
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 229910021653 sulphate ion Inorganic materials 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 5
- 159000000000 sodium salts Chemical class 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 3
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- -1 alkali-metal salts Chemical class 0.000 description 2
- YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- QMMRZOWCJAIUJA-UHFFFAOYSA-L nickel dichloride Chemical compound Cl[Ni]Cl QMMRZOWCJAIUJA-UHFFFAOYSA-L 0.000 description 2
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 2
- 235000010234 sodium benzoate Nutrition 0.000 description 2
- 239000004299 sodium benzoate Substances 0.000 description 2
- NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 2
- 235000009529 zinc sulphate Nutrition 0.000 description 2
- 239000011686 zinc sulphate Substances 0.000 description 2
- HSQFVBWFPBKHEB-UHFFFAOYSA-N 2,3,4-trichlorophenol Chemical compound OC1=CC=C(Cl)C(Cl)=C1Cl HSQFVBWFPBKHEB-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- 229910021586 Nickel(II) chloride Inorganic materials 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000008346 aqueous phase Substances 0.000 description 1
- 229940120693 copper naphthenate Drugs 0.000 description 1
- LABRFZDGWLJDJS-UHFFFAOYSA-N copper;2,3,4,5,6-pentachlorophenol Chemical compound [Cu].OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl LABRFZDGWLJDJS-UHFFFAOYSA-N 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 230000002363 herbicidal effect Effects 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- YFPNAQYEHBHHHI-UHFFFAOYSA-M sodium;2,3,4-trichlorophenolate Chemical compound [Na+].[O-]C1=CC=C(Cl)C(Cl)=C1Cl YFPNAQYEHBHHHI-UHFFFAOYSA-M 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/24—Halogenated derivatives
- C07C39/44—Metal derivatives of an hydroxy group bound to a carbon atom of a six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
- C07F1/005—Compounds containing elements of Groups 1 or 11 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F3/00—Compounds containing elements of Groups 2 or 12 of the Periodic Table
- C07F3/003—Compounds containing elements of Groups 2 or 12 of the Periodic Table without C-Metal linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/06—Aluminium compounds
- C07F5/069—Aluminium compounds without C-aluminium linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07G—COMPOUNDS OF UNKNOWN CONSTITUTION
- C07G99/00—Subject matter not provided for in other groups of this subclass
Definitions
- the compounds mentioned can be produced in a technically easier and simpler manner by mixing an aqueous solution of about 1 mol of a watersoluble salt of a polychlorophenol and of about 1 mol of a water soluble salt of a higher carboxylic acid with an aqueous solution of an equivalent amount of a watersoluble salt of a polyvalent metal at room temperature or slightly elevated temperatures, for example, up to about 60 C., and optionally in the presence of an organic solvent.
- the metal compound to be produced precipitates out as a crystalline material after the addition of the third reaction component. It the reaction is carried out in the presence of an organic solvent a solu- .iOl'l of the compound to be produced is obtained directly n the organic solvent which only needs to be separated from the aqueous phase.
- water-soluble salts of the polychloro- )henols are the alkali-metal salts of 2,4-dichlorophenol, 1,4,5- and 2,4,6-trichlorophenol, tetrachlorophenol, and :specially pentachlorophenol, such as the lithium, sodium mcl potassium salts.
- water-soluble salts of higher carboxylic lCldS are the alkali-metal salts of benzoic acid, p-chloroienzoic acid, lauric acid, oleic acid, stearic acid, naphhenic acid and tall oil fatty acids.
- water-soluble salts of polyvalent metals here may be mentioned, by way of example, zinc chloide and sulphate, cadmium chloride and sulphate, coper chloride and sulphate, barium chloride, aluminum hloride and sulphate, cerium sulphate, lead nitrate, man- :anesc chloride and sulphate and nickel chloride and sulhate.
- Organic solvents which may be used if desired, are, for xample, solvent naphtha, test benzine and light coal tar ii.
- Example I 28.8 grams (0.1 mol) sodium pentachlorophenolate and 25.5 grams (0.1 mol) sodium naphthenate are dissolved in 250 milliliters water. A solution of 28.7 grams (0.1 mol) crystalline zinc sulphate in milliliters water is added at room temperature with stirring to this solution. The yield is quantitative. The white precipitate is very easily soluble in light coal tar oil (B.P. 200300 C.) and is about 5 percent soluble in solvent naphtha.
- Example 2 43.2 grams (0.15 mol) sodium pentachlorophenolate and 38.5 grams (0.15 mol) sodium naphthenate are dissolved in 400 milliliters water. A solution of 25 grams (about 0.1 mol) crystalline aluminum chloride in 200 milliliters water is added at room temperature to this mixture. The precipitation is quantitative. The white precipitate is soluble to about 6 percent in solvent naphtha and test benzine. It is very easily soluble in light coal tar oil.
- Example 3 28.8 grams sodium pentachlorophenolate and 31.7 grams sodium oleate (approximately 0.11 mol) are dissolved in 300 milliliters water. A solution of 25 grams copper sulphate (0.1 mol CuSO .5H O) in 100 milliliters water is added at room temperature to this mixture. The reaction proceeds quantitatively. The blackbrown precipitate is about 20 percent soluble in light coal tar oil and about 15 percent soluble in solvent naphtha or test benzine.
- Example 4 28.8 grams sodium pentachlorophenolate and 14.5 grams sodium benzoate (0.1 mol) are dissolved in 300 milliliters water. A solution of 25 grams copper sulphate in 100 milliliters water is added at room temperature to this mixture. The bright red-brown precipitate is about 20 percent soluble in light coal tar oil.
- Example 5 44.0 grams sodium trichlorophenolate (0.2 mol) and 51 grams sodium naphthenate (0.2 mol) are dissolved in 400 milliliters water. 700 milliliters solvent are added to this mixture and a solution of 50 grams copper sulphate (0.2 mol) in 200 milliliters water allowed to run in with stirring at room temperature. The reaction product is completely soluble in the above mentioned amount of solvent naphtha.
- Example 6 28.8 grams sodium pentachlorophenolate and 25.5 grams sodium naphthenate are dissolved in 300 milliliters water. milliliters light coal tar oil (HP. 200- 300 C.) are added to this mixture and then a solution of 25 grams copper sulphate and 100 milliliters water is allowed to run in with stirring at room temperature. The reaction product is completely soluble in the coal tar oil. An approximately 30 percent solution of pentachlorophenol-copper naphthenate is obtained.
- a process for the production of a compound of a polyvalent metal, a polychlorophenol, and a higher carboxylic acid which comprises mixing an aqueous solution of approximately equimolecular amounts of a water-soluble salt of a polychlorophenol selected from the group consisting of the lithium, sodium, and potassium salts of 2,4-dichlorophenol, 2,4,5- and 2,4,6-trichlorophenol, tetrachlorophenol, and pentachlorophenol, a water-soluble salt of a higher carboxylic acid selected from the group consisting of the lithium, sodium, and potassium salts of benzoic acid, p-chlorobenzoic acid, lauric acid, oleic acid, stearic acid, naphthenic acid and tall oil fatty acids, and an aqueous solution of an approximately equivalent amount of a Water-soluble salt of a polyvalent metal selected from the group consisting of zinc, cadmium, copper, aluminum, manganese and nickel chlorides and sulphates,
- a process for the production of a compound of a polyvalent metal, a polychlorophenol and a higher carboxylic acid wherein an aqueous solution of 1 mol sodium pentachlorophenolate and 1 mol sodium naphthenate is mixed with an aqueous solution of 1 mol zinc 5 sulphate.
- a process for the production of a compound of a polyvalent metal, a polychlorophenol, and a higher carboxylic acid wherein an aqueous solution of 1 mol sodium pentachlorophenolate and 1 mol sodium naphthenate in admixture with light coal tar oil is mixed with an aqueous solution of 1 mol copper sulphate.
- a process for the production of a compound of a polyvalent metal, a polychlorophenol, and a higher carboxylic acid wherein an aqueous solution of 1 mol sodium pentachlorophenolate and 1 mol sodium naphthenate is mixed with an aqueous solution of 1 mol aluminum chloride.
- a process for the production of a compound of a polyvalent metal, a polychlorophenol, and a higher car- 20 hoxylic acid wherein an aqueous solution of 1 mol sodium pentachlorophenolate and 1 mol sodium oleate is mixed with an aqueous solution of 1 mol copper sulphate.
- a process for the production of a compound of a polyvalent metal, a polychlorophenol, and a higher car- 25 l-oxylic acid wherein an aqueous solution of 1 mol sodium pentachlorophenolate and 1 mol sodium benzoate is mixed with an aqeuous solution of 1 mol copper sulphate.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF28634A DE1172686B (de) | 1959-06-06 | 1959-06-06 | Verfahren zur Herstellung von Mischsalzen aus mehrwertigen Metallen, Polychlorphenolen und hoehermolekularen Carbonsaeuren |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3064019A true US3064019A (en) | 1962-11-13 |
Family
ID=7092960
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US32118A Expired - Lifetime US3064019A (en) | 1959-06-06 | 1960-05-27 | Process for the production of compounds of polyvalent metals with polychlorophenols and higher carboxylic acids |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3064019A (en(2012)) |
| BE (1) | BE590809A (en(2012)) |
| DE (1) | DE1172686B (en(2012)) |
| FR (1) | FR1268492A (en(2012)) |
| GB (1) | GB895440A (en(2012)) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3661550A (en) * | 1969-08-22 | 1972-05-09 | Texaco Trinidad | Process for making micronutrient naphthenate compositions |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1994002A (en) * | 1932-05-02 | 1935-03-12 | Dow Chemical Co | Zinc 2.4.5-trichlorophenolate |
| US2890232A (en) * | 1956-05-31 | 1959-06-09 | Swift & Co | Manufacture of metal soaps |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE567276A (en(2012)) * | 1957-05-16 |
-
0
- BE BE590809D patent/BE590809A/xx unknown
-
1959
- 1959-06-06 DE DEF28634A patent/DE1172686B/de active Pending
-
1960
- 1960-05-13 FR FR827061A patent/FR1268492A/fr not_active Expired
- 1960-05-27 GB GB18912/60A patent/GB895440A/en not_active Expired
- 1960-05-27 US US32118A patent/US3064019A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1994002A (en) * | 1932-05-02 | 1935-03-12 | Dow Chemical Co | Zinc 2.4.5-trichlorophenolate |
| US2890232A (en) * | 1956-05-31 | 1959-06-09 | Swift & Co | Manufacture of metal soaps |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3661550A (en) * | 1969-08-22 | 1972-05-09 | Texaco Trinidad | Process for making micronutrient naphthenate compositions |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1172686B (de) | 1964-06-25 |
| FR1268492A (fr) | 1961-08-04 |
| GB895440A (en) | 1962-05-02 |
| BE590809A (en(2012)) |
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